Fungicidal active substance combinations

ABSTRACT

Novel active compound combinations comprising a compound of the formula (I)                    
     and known fungicidally active compounds, and their use for controlling phytopathogenic fungi, are described.

This application is a divisional application of U.S. application Ser.No. 09/319,400, filed on Jun. 2, 1999 now U.S. Pat. No. 6,191,128, whichis a 371 of PCT/EP97/06616, filed Nov. 27, 1997.

TECHNICAL FIELD OF THE INVENTION

The present application relates to novel active compound combinationswhich are highly suitable for controlling phytopathogenic fungi andwhich comprise a compound of the formula (I)

and other known fungicidally, active compounds.

BACKGROUND OF THE INVENTION

It is already known that the compound of the formula (I) has fungicidalproperties (DE-19 602 095). The activity of this compound is good;however, it is not always satisfactory at low application rates.

Furthermore, it is already, known that a large number of azolederivatives, aromatic carboxylic acid derivatives, morpholine compoundsand other heterocycles can be employed for controlling fungi (cf. K. H.Buchel “Pflanzenschutz und Schädlingsbekämpfung”, pages 87, 136, 140,141 and 146 to 153, Georg Thieme Verlag. Stuttgart 1977). However, theactivity of the compounds in question is not always satisfactor at lowapplication rates.

DETAILED DESCRIPTION OF THE INVENTION

The present invention, accordingly, provides the novel active compoundcombinations comprising a compound of the formula (I)

and at least one mixing partner

(A) Antracol (propineb) and/or

(B) Euparene (dichlorofluanide) and/or Euparene M (tolylfluatide) and/or

(C) bitertanol and/or

(D) tebuconazole and/or

(E) triadimefon and/or

(F) triadimenol and/or

(G) imidacloprid and/or

(H) Sumisclex and/or

(II) mancozeb and/or

(K) folpet (Phaltan) and/or

(L) dimetomorph and/or

(M) cymoxanil and/or

(N) metalaxyl and/or

(O) Aliette (fosetyl-Al) and/or

(P) famoxadone and/or

(Q) pyrimethanil and/or

(R) cyprodinyl and/or

(S) mepanipyrim and/or

(T) kresoxim-methyl and/or

(U) azoxystrobin and/or

(V) epoxiconazole and/or

(W) metconazole and/or

(X) fluquinconazole and/or

(Y) fludioxonil and/or

(Z) fenpiclonil and/or

(α) guazatine and/or

(β) Bione and/or

(χ) 1-methylethyl[2-methyl-1-[[[1-(4-methylphenyl)ethyl]amino]carbonyl]-propyl]carboxylicacid and/or

(δ)8-t-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-1,4-dioxaspiro[5.4]-decaneand/or

(ε) 2,3-dichloro-4-(1-methylcyclohexylcarbonylamino)-phenol and/or

(ω)N-(R)-[1-(4-chloro-phenyl)-ethyl]-2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropane-carboxamideand/or

(π) fluazinam and/or

(θ) captan and/or

(ρ) Monceren (pencycuron) and/or

(σ) fenpiclonil

which have very good fungicidal properties which complement each othersynergistically.

The active compound of the formula (I) is known (DE-19 602 095). Theother components which are present in the combinations according to theinvention are also known.

In addition to the active compound of the formula (I), the activecompound combinations according to the invention comprise at least oneactive compound from the compounds (A) to (σ). However, furtherfungicidally active additives may additionally be present.

The synergistic effect is particularly pronounced when the activecompounds in the active compound combinations according to the inventionare present in certain weight ratios. However, the weight ratios of theactive compounds in the active compound combinations can be variedwithin relatively broad ranges. In general, there are 0.01 to 50,preferably 0.25 to 20, parts by weight of the active compounds (A) to(σ) per part by weight of active compound of the formula (I).

In particular, there are the stated parts by weight of the followingmixing partners per part by weight of the compound of the formula (I):

(A)  1:1 to 1:50 preferably  1:5 to 1:20, (B)  1:1 to 1:50 preferably 1:5 to 1:20, (C) 10:1 to 1:10 preferably 5:1 to 1:5, (D) 10:1 to 1:10preferably 5:1 to 1:5, (E) 10:1 to 1:10 preferably 5:1 to 1:5, (F) 10:1to 1:10 preferably 5:1 to 1:5, (G) 20:1 to 1:20 preferably 10:1 to 1:10,(H) 10:1 to 1:10 preferably 5:1 to 1:5, (II)  1:1 to 1:50 preferably 1:5 to 1:20, (K)  1:1 to 1:50 preferably  1:5 to 1:20, (L) 10:1 to 1:10preferably 5:1 to 1:5, (M) 10:1 to 1:10 preferably 5:1 to 1:5, (N) 10:1to 1:10 preferably 5:1 to 1:5, (O) 10:1 to 1:50 preferably  1:1 to 1:10,(P) 10:1 to 1:10 preferably 5:1 to 1:5, (Q)  5:1 to 1:20 preferably  1:1to 1:10, (R)  5:1 to 1:20 preferably  1:1 to 1:10, (S)  5:1 to 1:20preferably  1:1 to 1:10, (T) 10:1 to 1:10 preferabiy 5:1 to 1:5, (U)10:1 to 1:10 preferably 5:1 to 1:5, (V) 10:1 to 1:10 preferably 5:1 to1:5, (W) 10:1 to 1:10 preferably 5:1 to 1:5, (X) 10:1 to 1:10 preferably5:1 to 1:5, (Y) 10:1 to 1:10 preferably 5:1 to 1:5, (Z) 10:1 to 1:10preferably 5:1 to 1:5, (α) 10:1 to 1:10 preferably 5:1 to 1:5, (β) 50:1to 1:50 preferably 20:1 to 1:10, (χ) 10:1 to 1:10 preferably 5:1 to 1:5,(δ) 10:1 to 1:20 preferably  5:1 to 1:10, (ε) 10:1 to 1:10 preferably5:1 to 1:5, (ω) 10:1 to 1:10 preferably 5:1 to 1:5, (π) 10:1 to 1:10preferably 5:1 to 1:5, (θ)  5:1 to 1:50 preferably  1:1 to 1:20, (ρ)10:1 to 1:10 preferably 4:1 to 1:4, (σ) 10:1 to 1:10 preferably 4:1 to1:4

The active compound combinations according to the invention have verygood fungicidal properties and can be employed in particular forcontrolling phytopathogenic fungi, such as Plasmodiophoromycetes,Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetesand Deuteromycetes, etc.

The active compound combinations according to the invention areparticularly suitable for controlling cereal diseases, such as Erysiphe,Cochliobolus, Pyrenophora, RPhynchosporium, Septoria spp., Fusariumspp., Pseudocercosporella and Leptosphaeria, and for controlling fungalinfections of non-cereal crops such as wine, fruit, vegetables, forexample Phytophthora, Plasmopara, Pythium, and powdery mildew fungi suchas, for example, Sphaerotheca or Uncinula, and causative organisms ofleaf spot such as Venturia, Altemaria and Septoria, and Rhizoctonia,Botrytis, Sclerotinia and Sclerotium.

The fact that the active compound combinations are well tolerated byplants at the concentrations required for controlling plant diseasespermits the treatment of aerial parts of plants, of propagation stockand seeds, and of the soil.

The active compound combinations according to the invention can beconverted to the customary formulations, such as solutions, emulsions,suspensions, powders, foams, pastes, granules, aerosols andmicroencapsulations in polymeric substances and in coating compositionsfor seeds, and ULV formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds or active compound combinations with extenders,that is liquid solvents, liquefied gases under pressure, and/or solidcarriers, optionally with the use of surfactants, that is emulsifiersand/or dispersants, and/or foam formers. If the extender used is water,it is also possible to use, for example, organic solvents as auxiliarysolvents. Essentially, suitable liquid solvents include: aromatics suchas xylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water. Liquefied gaseous extenders or carriers areto be understood as meaning liquids which are gaseous at ambienttemperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons and butane, propane,nitrogen and carbon dioxide. Suitable solid carriers are: for exampleground natural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as finely divided silica, alumina and silicates. Suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks. Suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates. Suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and prussian blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

In the formulations, the active compound combinations according to theinvention can be present as a mixture with other known active compoundssuch as fungicides, insecticides, acaricides and herbicides, and asmixtures with fertilizers or plant growth regulators.

The active compound combinations can be used as such, in the form oftheir formulations or as the use forms prepared therefrom, such asready-to-use solutions, emulsifiable concentrates, emulsions,suspensions, wettable powders, soluble powders and granules.

They are used in the customary manner, for example by watering,spraying, atomizing, scattering, spreading, and as a powder for dry seedtreatment, a solution for seed treatment, a water-soluble powder forseed treatment, a water-soluble powder for slurry treatment, or byencrusting.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a relatively wide range. Ingeneral, they are between 1 and 0.0001% by weight, preferably between0.5 and 0.001%.

In the treatment of seeds, amounts of 0.001 to 50 g of active compoundper kilogram of seeds are generally required, preferably 0.01 to 10 g.

In the treatment of the soil, active compound concentrations of 0.00001to 0.1% by weight, preferably of 0.0001 to 0.02% by weight, are requiredat the site of action.

The good fungicidal, synergistic activity of the active compoundcombinations according to the invention is evident from the examplesbelow. While the individual active compounds exhibit weaknesses withregard to the fungicidal activity, the combinations have an activitywhich exceeds a simple addition of activities.

A synergistic effect of fungicides is always present when the fungicidalactivity of the active compound combinations exceeds the total of heactivities of the active compounds when applied individually.

The expected activity for a given combination of two active compoundscan be calculated as follows (cf. Colby, S. R., “Calculating Synergisticand Antagonistic Responses of Fierbicide Combinations”, Weeds 15, pages20-22, 1967):

If

X is the efficacy expressed in % of the untreated control when applyingactive compound A in a concentration of m ppm,

Y is the efficacy expressed in % of the untreated control when applyingactive compound B at a concentration of n ppm,

E is the expected efficacy expressed in % of the untreated control whenapplying the active substances A and B at a concentration of m and nppm, respectively, then $E = {X + Y - \frac{X \cdot Y}{100}}$

If the actual fungicidal activity exceeds the calculated value, then theactivity of the combination is superadditive, i.e. a synergistic effectexists. In this case, the efficacy which was actually observed must begreater than the value for the expected efficacy (E) calculated from theabovementioned formula:

EXAMPLE 1 Phytophthora Test (Tomato)/Protective

To test for protective activity, young plants are sprayed with thecommercial active compound preparation at the stated application rate.After the spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Phytophthora infestans. The plants thenremain in an incubation cabin at about 20° C. and 100% relativeatmospheric humidity.

Evaluation is carried out 3 days after the inoculation. 0% means anefficacy corresponding to that of the control, and an efficacy of 100%means that no infection is observed.

The good fungicidal activity of the active compound combinationsaccording to the invention is evident from the example below. While theindividual active compounds exhibit weaknesses with regard to thefungicidal activity, the combinations have an activity which exceeds asimple addition of activities.

A synergistic effect of fungicides is always present when the fungicidalactivity of the active compound combinations exceeds the total of theactivities of the active compounds when applied individually.

The expected activity for a given combination of two active compoundscan be calculated as follows (cf. Colby, S. R., “Calculating Synergisticand Antagonistic Responses of Herbicide Combinations”, Weeds 15, pages20-22, 1967):

If

X is the efficacy expressed in % of the untreated control when applyingactive compound A in a concentration of rn ppm,

Y is the efficacy expressed in % of the untreated control when applyingactive compound B at a concentration of n ppm,

E is the expected efficacy expressed in % of the untreated control whenapplying the active substances A and B at a concentration of m and nppm, respectively, then $E = {X + Y - \frac{X \times Y}{100}}$

If the actual fungicidal activity exceeds the calculated value, then theactivity of the combination is superadditive, i.e. a synergistic effectexists. In this case, the efficacy which was actually observed must begreater than the value for the expected efficacy (E) calculated from theabovementioned formula.

The table below clearly shows that the observed activity of the activecompound combination according to the invention is greater than thecalculated activity, i.e. a synergistic effect is present.

TABLE 1 Phytophtora test (tomato)/protective Active compound Activecompound application rate in g/ha % efficacy (I) 0.5  9

(χ) 0.5 20

Racemic amide of L-valine Mixture according to the invention: Activecompound Expected value, application rate calculated using Mixing ratioin g/ha Actual efficacy Colby's formula (I) 0.5 1:1 + 77 27 (χ) 0.5Active compound Active compound application rate in g/ha % efficacy (I)5 45

Tebuconazole (D) 5 26

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 5 1:1 + 84 59 (D) 5 Active compound Active compoundapplication rate in g/ha % efficacy (I) 5 45

Triadimenol (F) 5  0

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 5 1:1 + 72 45 (F) 5 Active compound Active compoundapplication rate in g/ha % efficacy (I) 5 45

(ε) 5 14

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 5 1:1 + 82 53 (ε) 5 Active compound Active compoundapplication rate in g/ha % efficacy (I) 5 45

(ω) 5  3

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 5 1:1 + 71 47 (ω) 5 Active compound Active compoundapplication rate in g/ha % efficacy (I) 5 45

(H) 5 34

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 5 + 1:1 + 75 64 Procymidone 5 Active compound Activecompound application rate in g/ha % efficacy (I) 5 45

Mancozeb (II) 50  54

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 5 + 1:10 + 89 75 Mancozeb (II) 5 Active compoundActive compound application rate in g/ha % efficacy (I) 1 20

Phaltan (K) 10  27

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 1 + 1:10 + 74 42 Phaltan 10  Active compound Activecompound application rate in g/ha % efficacy (I) 1 20

Dimetomorph (L) 1  0

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 1 + 1:1 + 49 20 Dimetomorph (L) 1 Active compoundActive compound application rate in g/ha % efficacy (I) 5 45

Cymoxanil (M) 5 12

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 5 + 1:1 + 78 52 Cymoxanil 5 Active compound Activecompound application rate in g/ha % efficacy (I) 5 45

Metalaxyl (N) 5  1

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 5 + 1:1 + 62 46 (N) 5 Active compound Activecompound application rate in g/ha % efficacy (I) 5 45

Fluazinam (π) 5 11

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 5 + 1:1 + 85 51 Fluazinam (π) 5 Active compoundActive compound application rate in g/ha % efficacy (I) 5 45

Cyprodinyl (R) 5  0

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 5 + 1:1 + 62 45 Cyprodinyl 5 Active compound Activecompound application rate in g/ha % efficacy (I) 1 20

Kresoxime- 1 14 methyl (T)

Mixture according to the invention: Active compound Expected value,application rate calculated using Mixing ratio in g/ha Actual efficacyColby's formula (I) 1 + 1:1 + 64 31 Kresoxime- 1 methyl (T) Activecompound Active compound application rate in g/ha % efficacy (I) 5 45

Bendicar 5  0 (Bion) (β) Mixture according to the invention: Activecompound Expected value, application rate calculated using Mixing ratioin g/ha Actual efficacy Colby's formula (I) 5 + 1:1 + 54 45 Bendicar 5

EXAMPLE 2

Sphaerotheca Test (Cucumber)/Protective

To test for protective activity, young plants are sprayed with thecommercial active compound preparation at the stated application rate.After the spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Sphaerotheca fuliginea. The plants thenremain in a greenhouse at about 23° C. and about 70% relativeatmospheric humidity.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy corresponding to that of the control, and an efficacy of 100%means that no infection is observed.

The good fungicidal activity of the active compound combinationsaccording to the invention is evident from the example below. While theindividual active compounds exhibit weaknesses with regard to thefungicidal activity, the combinations have an activity which exceeds asimple addition of activities.

A synergistic effect of fungicides is always present when the fungicidalactivity of the active compound combinations exceeds the total of theactivities of the active compounds when applied individually.

The expected activity for a given combination of two active compoundscan be calculated as follows (cf. Colby, S. R., “Calculating Synergisticand Antagonistic Responses of Herbicide Combinations”, Weeds 15, pages20-22, 1967):

If

X is the efficacy expressed in % of the untreated control when applyingactive compound A in a concentration of m ppm,

Y is the efficacy expressed in % of the untreated control when applyingactive compound B at a concentration of n ppm,

E is the expected efficacy expressed in % of the untreated control whenapplying the active substances A and B at a concentration of m and nppm, respectively, then $E = {X + Y - \frac{X \times Y}{100}}$

If the actual fungicidal activity exceeds the calculated value, then theactivity of the combination is superadditive, i.e. a synergistic effectexists. In this case, the efficacy which was actually observed must begreater than the value for the expected efficacy (E) calculated from theabovementioned formula.

The table below clearly shows that the observed activity of the activecompound combination according to the invention is greater than thecalculated activity, i.e. a synergistic effect is present.

TABLE 2 Sphaerotheca test (cucumber)/protective Active compound Activecompound application rate in g/ha % efficacy (I)

2.5 22 Propineb (A)

25 45 _(n)= >1 Mixture according to the invention: Active compoundExpected value, application rate calculated using Mixing ratio in g/haActual efficacy Colby's formula (I) 2.5 + 1:10 + 77 56 Propineb 25Sphaerotheca test (cucumber)/protective Active compound Active compoundapplication rate in g/ha % efficacy (I)

2.5 22 Dichlorofluanid (B1)

25 20 Mixture according to the invention: Active compound Expectedvalue, application rate calculated using Mixing ratio in g/ha Actualefficacy Colby's formula (I) 2.5 + 1:10 + 57 38 Dichlorofluanid 25Sphaerotheca test (cucumber)/protective Active compound Active compoundapplication rate in g/ha % efficacy (I)

2.5 22 Tolyfluanid (B2)

25 22 Mixture according to the invention: Active compound Expectedvalue, application rate calculated using Mixing ratio in g/ha Actualefficacy Colby's formula (I) 2.5 + 1:10 + 57 39 Tolylfluanid 25Sphaerotheca test (cucumber)/protective Active compound Active compoundapplication rate in g/ha % efficacy (I)

2.5 22 Bitertanol (C)

2.5 20 Mixture according to the invention: Active compound Expectedvalue, application rate calculated using Mixing ratio in g/ha Actualefficacy Colby's formula (I) 2.5 + 1:1 + 50 38 Bitertanol 2.5Sphaerotheca test (cucumber)/protective Active compound Active compoundapplication rate in g/ha % efficacy (I)

2.5 22 Triadimefon (E)

2.5 30 Mixture according to the invention: Active compound Expectedvalue, application rate calculated using Mixing ratio in g/ha Actualefficacy Colby's formula (I) 2.5 + 1:1 + 67 45 Triadimefon 2.5Sphaerotheca test (cucumber)/protective Active compound Active compoundapplication rate in g/ha % efficacy (I)

2.5 22 (δ)

2.5 10 Mixture according to the invention: Active compound Expectedvalue, application rate calculated using Mixing ratio in g/ha Actualefficacy Colby's formula (I) 2.5 + 1:1 + 70 30 (δ) 2.5 Sphaerotheca test(cucumber)/protective Active compound Active compound application ratein g/ha % efficacy (I)

2.5 22 Captan (θ)

12.5 0 Mixture according to the invention: Active compound Expectedvalue, application rate calculated using Mixing ratio in g/ha Actualefficacy Colby's formula (I) 2.5 + 1:5 + 63 22 Captan 12.5 Sphaerothecatest (cucumber)/protective Active compound Active compound applicationrate in g/ha % efficacy (I)

2.5 22 Pyrimethanil (Q)

12.5 10 Mixture according to the invention: Active compound Expectedvalue, application rate calculated using Mixing ratio in g/ha Actualefficacy Colby's formula (I) 2.5 + 1:5 + 57 30 Pyrimethanil 12.5Sphaerotheca test (cucumber)/protective Active compound Active compoundapplication rate in g/ha % efficacy (I)

2.5 22 Azoxystrobin (U)

2.5 57 Mixture according to the invention: Active compound Expectedvalue, application rate calculated using Mixing ratio in g/ha Actualefficacy Colby's formula (I) 2.5 + 1:1 + 83 66 Azoxystrobin 2.5

EXAMPLE 3 Botrtis Test (Beans)/Protective

To test for protective activity, young plants are sprayed with thecommercial active compound preparation at the stated application rate.After the spray coating has dried on, 2 small pieces of agar coveredwith Botrytis cinerea are placed on each leaf. The inoculated plants areplaced in a darkened chamber at about 20° C. and 100% relativeatmospheric humidity.

Two days after the inoculation, the size of the infected spots on theleaves is evaluated. 0% means an efficacy corresponding to that of thecontrol, and an efficacy of 100% means that no infection is observed.

The good fungicidal activity of the active compound combinationsaccording to the invention is evident from the example below. While theindividual active compounds exhibit weaknesses with regard to thefungicidal activity, the combinations have an activity which exceeds asimple addition of activities.

A synergistic effect of fungicides is always present when the fungicidalactivity of the active compound combinations exceeds the total of theactivities of the active compounds when applied individually.

The expected activity for a given combination of two active compoundscan be calculated as follows (cf. Colby, S. R., “Calculating Synergisticand Antagonistic Responses of Herbicide Combinations”, Weeds 15, pages20-22, 1967):

If

X is the efficacy expressed in % of the untreated control when applyingactive compound A in a concentration of m ppm,

Y is the efficacy expressed in % of the untreated control when applyingactive compound B at a concentration of n ppm,

E is the expected efficacy expressed in % of the untreated control whenapplying the active substances A and B at a concentration of m and nppm, respectively, then $E = {X + Y - \frac{X \times Y}{100}}$

If the actual fungicidal activity exceeds the calculated value, then theactivity of the combination is superadditive, i.e. a synergistic effectexists. In this case, the efficacy which was actually observed must begreater than the value for the expected efficacy (E) calculated from theabovementioned formula.

The table below clearly shows that the observed activity of the activecompound combination according to the invention is greater than thecalculated activity, i.e. a synergistic effect is present.

TABLE 3 Botrytis test (beans)/protective Active compound Active compoundapplication rate in g/ha % efficacy

 50 15 fosethyl-A1 (O)

250  4 × 3 × Al Mixture according to the invention: Active compoundExpected value, application rate calculated using Mixing ratio in g/haActual efficacy Colby's formula (I)  50 + 1:5 + 55 18 fosethyl-A1 250

EXAMPLE 4 Fusarlium nivale Test (Triticale)/Seed Treatment

The active compounds are applied as a dry seed dressing. This isprepared by extending the respective active compound with ground mineralto give a finely pulveruient mixture which ensues uniform distributionon the seed surface.

To dress the seed, the infected seed together with the seed dressing isshaken for 3 minutes ini a sealed glass flask.

2×100 corns of triticale are sown at a depth of 1 cm in standard soiland cultivated in a greenhouse at a temperature of about 10° C. and arelative atmospheric humidity of about 95% in seed trays which receive alight regimen of 15 hours per day.

About 3 weeks after sowing, the plants are evaluated for symptoms ofsnow mould. 0% means an efficacy which corresponds to that of theuntreated control, while an efficacy of 100% means that no disease isobserved.

TABLE 4 Fusarium nivale test (triticale)/seed treatment Active compoundapplication rate Active compound in mg/kg of seed Efficacy in %

75 93 (Tebuconazole) (O) 25 89

25 20 (Triadimenol) (F) 25 20

25 52 (Pencycuron) P 25 29

(Fenpiclonil) V 75 67

(Fludioxonil) (Y) 75 92

(I) 12.5 97 (V) +12.5 (I) 12.5 97 (F) +12.5 (I) 12.5 93 +moncerene +12.5(I) 37.5 100 (V) +37.5 (I) 37.5 99 (Y) +37.5

EXAMPLE 5 Rihzoctonia solani Test (Cotton)/Seed Treatment

The active compounds are applied as dry seed dressing. This is preparedby extending the respective active compound with ground mineral to givea finely pulverulent mixture which ensures uniform distribution on theseed surface.

To dress the seed, the infected seed together with the seed dressing isshaken for 3 minutes in a scaled glass flask.

2×50 corns of seed are sown at a depth of 2 cm into standard soil whichis infected with Rhizoctonia solani, and the seeds are cultivated in agreenhouse at a temperature of about 22° C. in seed trays which receivea light regimen of 15 hours per day.

Evaluation is carried out after 8 days. 0% means an efficacy whichcorresponds to that of the untreated control, while an efficacy of 100%means that no disease is observed.

TABLE 5 Rhizoctonia solani test (cotton)/seed treatment Active compoundapplication rate Active compound in mg/kg of seed Efficacy in % (I) 7516

(Triadimenol) (F) 75 48

Mixture according to the invention (I) 37.5 (F) +37.5 63

EXAMPLE 6 Erysiphe Test (Barley)/Curative

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for curative activity, young plants are dusted with spores ofErysiphe graminis f.sp. hordei. 48 hours after the inoculation, theplants are sprayed with the preparation of active compound at the statedapplication rate.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80%, in order to promotethe development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE 6 Erysiphe test (barley)/curative Active compound application ratein Active compound g/ha Efficacy in % Known: (I) 25 75 12.5 33 6.25  0(D) 25 83 6.25 33 (F) 6.25 67 (V) 12.5 92 (W) 6.25 33 (T) 12.5 67 (δ)6.25  0 Mixtures according to the invention (I) + (D)  6.25 + 18.75 100 3.125 + 3.125 75 18.75 + 6.25  92 (I) + (F) 1.563 + 4.687 83 (I) + (T)6.25 + 6.25 75 3.125 + 9.375 83 9.375 + 3.125 83 (I) + (V) 6.25 + 6.25100  3.125 + 9.375 100  (I) + (W) 1.563 + 4.687 67 (I) + (δ) 3.125 +3.125 50 1.563 + 4.687 83

EXAMPLE 7 Erysiphe Test (Wheat)/Curative

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for curative activity, young plants are dusted with spores ofErysiphe graminis f.sp. tritici. 48 hours after the inoculation, theplants are sprayed with the preparation of active compound at the statedapplication rate.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80%, in order to promotethe development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE 7 Active compound application rate in Active compound g/haEfficacy in % Known: (I) 25 33 6.25  0 (T) 6.25  0 (R) 25 17 (Y) 25  0Mixtures according to the invention (I) + (T) 3.125 + 3.125 50 4.6875 +1.5625 50 (I) + (R) 12.5 + 12.5 75 18.75 + 6.25  50 (I) + (Y)  6.25 +18.75 50 18.75 + 6.25  50

EXAMPLE 8 Leptosphaeria nodorum Test (Wheat)/Curative

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for curative activity, young plants are sprayed with a conidiasuspension of Leptosplhaeria nodorum. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours andare then sprayed with the preparation of active compound at the statedapplication rate.

The plants are placed in a greenhouse at a temperature of about 15° C.and a relative atmospheric humidity of about 80%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE 8 Leptosphaeria nodorum test (wheat)/curative Active compoundapplication rate in Active compound g/ha Efficacy in % Known: (I) 12.562 6.25 62 (F) 6.25 25 (W) 12.5 25 (T) 12.5 50 (δ) 12.5 25 (R) 6.25 50Mixtures according to the invention (I) + (F) 4.6875 + 1.5625 75 (I) +(W) 9.375 + 3.125 75 (I) + (T) 9.375 + 3.125 75 (I) + (δ) 9.375 + 3.12575 (I) + (R) 1.5625 + 4.6875 75

EXAMPLE 9 Pyrenophora teres Test (Barley)/Curative

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for curative activity, young plants are sprayed with a conidiasuspension of Pyrenophora teres. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours. Theplants are subsequently sprayed with the preparation of active compoundat the stated application rate.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80%.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE 9 Active compound application rate in Active compound g/haEfficacy in % Known: (I) 6.25 0 (F) 6.25 0 Mixtures according to theinvention (I) + (F) 4.6875 + 1.5625 50 

TABLE 10 Puccinia Test (Wheat)/Curative

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for curative activity, young plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours. Theplants are subsequently sprayed with the preparation of active compoundat the stated application rate.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80%, in order to promotethe development of rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE 10 Puccinia test (wheat)/curative Active compound application ratein Active compound g/ha Efficacy in % Known: (I) 6.25 67 (W) 6.25 50 (R)6.25 33 Mixtures according to the invention (I) + (W) 1.5625 + 4.6875 83(I) + (R) 3.125 + 3.125 75

EXAMPLE 11 Erysiphe Test (Wheat)/Protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f.sp. tritici.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80%, in order to promotethe development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE 11 Erysiphe test (wheat)/curative Active compound application ratein Active compound g/ha Efficacy in % Known: (I) 25 79 12.5 29 6.25  0(D) 6.25  0 (W) 6.25 43 (T) 25 86 (δ) 6.25 14 (R) 12.5  0 Mixturesaccording to the invention (I) + (D) 1.5625 + 4.6875 71 (I) + (W)4.6875 + 1.5625 57 (I) + (T)  6.25 + 18.75 93 (I) + (δ) 3.125 + 3.125 571.5625 + 4.6875 79 4.6875 + 1.5625 57 (I) + (R) 3.125 + 9.375 57

EXAMPLE 12 Leptosphaeria nodorum Test (Wheat)/Protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a sporesuspension of Leptosphaeria nodorum. The plants remain in an incubationcabin at 20EC and 100% relative atmospheric humidity for 48 hours.

The plants are placed in a greenhouse at a temperature of about 1 5° C.and a relative atmospheric humidity of 80%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE 12 Leptosphaeria nodorum test (wheat)/protective Active compoundapplication rate in {PRIVATE} Active compound g/ha Efficacy in % Known:(I) 6.25 25 (D) 6.25 25 (F) 6.25  0 (V) 6.25 50 (W) 6.25 50 (T) 6.25  0(δ) 6.25 25 (R) 6.25 25 (Y) 6.25 25 Mixtures according to the invention(I) + (D) 3.125 + 3.125  50 4.6875 + 1.5625  50 (I) + (F) 1.5625 +4.6875  50 1.5625 + 4.6875 100 (I) + (W) 3.125 + 3.125 100 (I) + (T)4.6875 + 1.5625  50 (I) + (δ) 1.5625 + 4.6875  75 4.6875 + 1.5625 100(I) + (R) 3.125 + 3.125 100 1.5625 + 4.6875 100 4.6875 + 1.5625 100(I) + (Y) 3.125 + 3.125  75 1.5625 + 4.6875 100 4.6875 + 1.5625 100

EXAMPLE 13 Puccinia Test (Wheat)/Protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of 80%, in order to promote thedevelopment of rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

TABLE 13 Puccinia test (wheat)/protective Active compound applicationrate in Active compound g/ha Efficacy in % Known: (I) 6.25 81 (D) 6.2538 (F) 6.25 13 (V) 6.25 81 (W) 6.25 75 (T) 6.25 25 (δ) 6.25 13 (R) 6.2513 (Y) 6.25 13 Mixtures according to the invention (I) + (D) 3.125 +3.125 94 1.5625 + 4.6875 94 4.6875 + 1.5625 88 (I) + (F) 3.125 + 3.12588 (I) + (V) 3.125 + 3.125 88 1.5625 + 4.6875 100  4.6875 + 1.5625 88(I) + (W) 3.125 + 3.125 100  1.5625 + 4.6875 88 4.6875 + 1.5625 100 (I) + (T) 4.6875 + 1.5625 100  (I) + (δ) 3.125 + 3.125 100  1.5625 +4.6875 94 4.6875 + 1.5625 100  (I) + (R) 3.125 + 3.125 94 1.5625 +4.6875 100  4.6875 + 1.5625 100  (I) + (Y) 3.125 + 3.125 100  1.5625 +4.6875 94 4.6875 + 1.5625 100 

What is claimed is:
 1. A fungicidal composition comprising asynergistically fungicidally effective amount of a combination of afirst component and a second component, wherein said first component isa compound of the formula (I)

and wherein said second component is selected from the group consistingof: Q pyrimethanil, R cyprodinyl, and S mepanipyrim.
 2. The compositionof claim 1, wherein the weight ratio of the first component to thesecond component 1:0.01 to 1:50.
 3. The composition of claim 1, whereinsaid second components is pyrimethanil.
 4. A process for preparing afungicidal composition comprising the step of mixing a synergisticamount the a composition according to claim 1 with extenders and/orsurfactants.
 5. A method for combating fungi, comprising applying to thefungi or their environment a fungicidally effective amount of asynergistic fungicidal composition according to claim 1.